This paper is aimed at giving an overview of possible cooling technologies for electrical machines and their assessment for aviation applications, e.g., fan or propeller drives. The most important demand for aircraft is the minimization of the drive system weight comprising electrical machine, power electronics, and the cooling system. The potential of aluminum winding an overview about several cooling technologies with the Rankine or Brayton cycle or utilizing the phase change of the cooling fluid is given. As an alternative approach, the cooling structure inside the machine is studied. A very interesting potential was discovered with direct slot cooling (DSC) removing the heat where it is produced and, thus, simplifying the cooling system effort and its weight. Since it is one of the most promising approaches, this cooling method is studied in depth. Furthermore, it can also be combined with one of the cooling technologies discussed above.